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Our top choices for Sheffield hotels

Wilder House Berkshires

Wilder House Berkshires
2.0 star property
Sheffield
9.8 out of 10, Exceptional, (41)
Escape to Sheffield's serene countryside in this inviting B&B. Enjoy complimentary WiFi, parking, and a delicious cooked-to-order weekend breakfast. Nearby attractions include the unique UFO Monument Park and peaceful Lime Kiln Farm Wildlife Sanctuary.

"The place is lovely, room is cozy, and the bed is comfy"
United States
Mark
The price is Rp2.717.874
Rp3.035.866 total
includes taxes & fees
30 Dec - 31 Dec
Wilder House Berkshires

Lakehouse Inn

Lakehouse Inn
4.0 star property
Lee
9.6 out of 10, Exceptional, (290)
Located in Lee, this inviting B&B offers kayaking adventures and a terrace with lakefront views. Wake up to a full breakfast each morning before exploring nearby attractions like The Mount and Wyndhurst Golf & Club. Helpful staff ensure a memorable stay.

"A charming inn in the center of the Berkshires."
United States
Danny
The price is Rp3.088.808
Rp3.622.708 total
includes taxes & fees
15 Jan - 16 Jan 2026
Lakehouse Inn

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (820)
This Lenox lodge combines comfort with convenience, just a short drive from Tanglewood Music Centre. The Club Room serves delicious American cuisine, while a welcoming bar and outdoor terrace enhance your stay. Kennedy Park and Pleasant Valley Wilderness Sanctuary await nearby.

"Easiest check in and out. Great food in dining room. "
United States
William
The price is Rp2.124.773
Rp2.373.371 total
includes taxes & fees
4 Jan - 5 Jan 2026
Berkshires Untold

the Alander

the Alander
2.5 star property
Copake
9.0 out of 10, Wonderful, (190)
Discover tranquility at this countryside lodge featuring the North Star restaurant serving American cuisine for dinner. Enjoy free WiFi and parking while exploring nearby Undermountain Golf Course and Copake Town Park. Rooms offer rainfall showerheads for extra comfort.

"The Alander has such a fun story, and was a great stay. We were just passing through for the night and it had everything we could need! It reminded me of Rosebud Motel group from Schitts Creek ;) if you know you know! Will definitely be staying again!"
United States
Jenna
The price is Rp2.348.780
Rp2.630.633 total
includes taxes & fees
27 Dec - 28 Dec
the Alander

The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1002)
"Old time charm and hot tub under the stars"
United States
Lori
The price is Rp2.518.050
Rp3.562.705 total
includes taxes & fees
14 Jan - 15 Jan 2026
The Red Lion Inn

Inn at Silver Maple Farm

Inn at Silver Maple Farm
3.0 star property
East Chatham
9.8 out of 10, Exceptional, (98)
Set amid East Chatham's natural beauty, this charming B&B welcomes guests with daily buffet breakfast and complimentary WiFi. Explore nearby Queechy Lake and Hand Hollow State Forest, with Albany Airport just 44 minutes away.

"Great stay, comfortable place"
United States
barry
The price is Rp2.164.233
Rp2.423.941 total
includes taxes & fees
4 Jan - 5 Jan 2026
Inn at Silver Maple Farm

The Inn at Stockbridge

The Inn at Stockbridge
4.0 star property
Lee
9.8 out of 10, Exceptional, (99)
Set in Lee, this B&B offers serene escapes with an outdoor pool and rejuvenating massages. Explore nearby National Shrine of Divine Mercy while enjoying free breakfast, WiFi, and parking. The 24-hour fitness centre and garden create a peaceful country getaway.

"Well-run and elegant property. "
United States
Steven
The price is Rp4.207.672
Rp4.935.122 total
includes taxes & fees
1 Jan - 2 Jan 2026
The Inn at Stockbridge

The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
3.5 star property
Lenox
9.0 out of 10, Wonderful, (1000)
Charming Cornell Inn offers a peaceful garden retreat within walking distance to Lenox attractions. Enjoy complimentary gourmet breakfast and unwind with a drink at the bar before retiring to comfortable rooms. Free WiFi and parking enhance your Berkshires getaway.

"The Inn was very nice and the staff was super friendly and attentive."
United States
Steven
The price is Rp2.888.080
Rp3.322.766 total
includes taxes & fees
2 Jan - 3 Jan 2026
The Cornell Inn, Lenox & The Berkshires

Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (165)
Located in a quiet area of Norfolk with free daily cooked-to-order breakfast, this B&B provides peaceful comfort near Haystack Mountain State Park. Enjoy complimentary WiFi and parking while the attentive staff ensures a relaxing countryside retreat.

"Courteous welcoming staff, amazing breakfast, and restful stay, highly recommend."
United States
Paulina
The price is Rp2.757.300
Rp3.170.895 total
includes taxes & fees
5 Jan - 6 Jan 2026
Blackberry River Inn

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel
3.0 star property
Lee
9.0 out of 10, Wonderful, (1000)
Enjoy panoramic lake vistas at this peaceful Lenox hotel, just 10 minutes from Tanglewood Music Centre. After working out in the 24-hour fitness centre, savour Indian cuisine at Mint restaurant while watching spectacular sunsets over the water.

"Room was clean and the staff was super friendly and helpful!"
United States
Ethan
The price is Rp1.683.736
Rp1.880.733 total
includes taxes & fees
13 Jan - 14 Jan 2026
The Black Swan Lee - Lenox, an Ascend Collection Hotel

Granville House

Granville House
3.0 star property
Housatonic
10.0 out of 10, Exceptional, (89)
Discover this charming B&B in Housatonic offering complimentary full breakfast, WiFi, and parking. Conveniently located near Monument Mountain and its reservation, this business-friendly getaway provides a perfect base for exploring local attractions.

"Outstanding all around!"
United States
Jonathan
The price is Rp3.758.048
Rp4.197.773 total
includes taxes & fees
29 Dec - 30 Dec
Granville House

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (795)
Set in Pittsfield near Guido's Marketplace and Herman Melville's Arrowhead, this lodge offers an indoor pool and hot tub for relaxation. Enjoy free WiFi and parking while staying in clean rooms. The helpful staff ensures a pleasant mountain getaway.

"Spacious room and loved pool and hot tub!"
United States
Deanna
The price is Rp1.656.626
Rp2.225.474 total
includes taxes & fees
11 Jan - 12 Jan 2026
Berkshire Mountain Lodge

Interlaken Inn & Resort

Interlaken Inn & Resort
3.5 star property
Lakeville
8.2 out of 10, Very good, (273)
Set on the greens in Lakeville, this inn provides a tranquil retreat with spa services, deep-tissue massages, and fitness options. Guests can enjoy meals at the restaurant, drinks at the bar, and easy access to local museums and tea rooms.

"It is so pretty and the views around the hotel were amazing. "
United States
Noraida
The price is Rp3.004.761
Rp3.455.559 total
includes taxes & fees
1 Jan - 2 Jan 2026
Interlaken Inn & Resort

33 Main

33 Main
4.0 star property
Lenox
10.0 out of 10, Exceptional, (74)
This charming bed and breakfast in Lenox offers a complimentary full breakfast daily. Enjoy free WiFi and parking while staying minutes from Lenox Library and The Bookshop. Pittsfield Municipal Airport is just an 11-minute drive away.

"Beautiful place. Wonderful owner and staff. Our stay there was a total delight."
United States
James
The price is Rp6.714.994
Rp7.500.649 total
includes taxes & fees
18 Jan - 19 Jan 2026
33 Main

East Rock Inn

East Rock Inn
2.0 star property
Great Barrington
9.4 out of 10, Exceptional, (36)
Outdoor enthusiasts will love this Great Barrington motel's access to hiking trails, kayaking, and mountain biking. Relax in the garden after exploring nearby Housatonic River and River Walk, with convenient free WiFi and parking throughout your stay.

"We had a great stay at East Rock Inn! Newly remodeled, clean room, comfortable bed, easy access to town. I will definitely stay there again."
United States
Laura
The price is Rp2.245.417
Rp2.508.130 total
includes taxes & fees
6 Jan - 7 Jan 2026
East Rock Inn

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
2.5 star property
Great Barrington
9.4 out of 10, Exceptional, (758)
Tranquil accommodation in Great Barrington offer soundproof rooms for undisturbed sleep. The helpful staff, complimentary breakfast, and free parking enhance your stay, while restaurants within walking distance and nearby Housatonic River provide convenient exploration options.

"Clean room, very courteous staff "
United States
Thomas
The price is Rp2.264.895
Rp2.529.888 total
includes taxes & fees
8 Jan - 9 Jan 2026
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

The Old Inn On The Green

The Old Inn On The Green
4.0 star property
Great Barrington
9.2 out of 10, Wonderful, (90)
Enjoy American cuisine by candlelight at the fine dining restaurant of this historic inn. A terrace and garden enhance the countryside charm, while the seasonal pool offers refreshing relaxation near Questing and New Marlborough Town Library.

"Beautiful Inn and outstanding chef"
United States
Catherine
The price is Rp5.116.985
Rp6.174.775 total
includes taxes & fees
28 Dec - 29 Dec
The Old Inn On The Green

Changing Times Boutique Country Lodging

Changing Times Boutique Country Lodging
3.5 star property
Craryville
10.0 out of 10, Exceptional, (109)
Rustic charm awaits at this Craryville B&B with free WiFi and parking. Explore the neighbouring hiking and biking trails or try kayaking. Lake Taghkanic State Park and West Beach are just moments away from this countryside haven.

"Great experience, looking forward to staying again."
United States
Greg
The price is Rp2.516.550
Rp2.818.536 total
includes taxes & fees
5 Jan - 6 Jan 2026
Changing Times Boutique Country Lodging

Hampton Terrace Inn

Hampton Terrace Inn
4.0 star property
Lenox
9.0 out of 10, Wonderful, (43)
Relax in this Lenox retreat with seasonal outdoor pool and tennis courts. Located just 5 minutes from Tanglewood Music Centre, with nearby access to Ventfort Hall Mansion and The Bookshop. Enjoy refreshments at the bar/lounge after exploring the charming grounds.

"Beautiful historic house in a great location. Responsive owner. Great visit!"
United States
Abby
The price is Rp3.672.485
Rp4.102.144 total
includes taxes & fees
2 Jan - 3 Jan 2026
Hampton Terrace Inn

The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (547)
Surrounded by natural attractions like Monument Mountain, this welcoming motel offers complimentary WiFi and parking. Daily housekeeping ensures comfort while the attentive staff enhances every stay in this charming Berkshires location.

"The check-in was easy and the room was ready and clean. It was nice having our dogs with us. "
United States
Maria
The price is Rp1.845.470
Rp2.061.390 total
includes taxes & fees
1 Jan - 2 Jan 2026
The Little Lion
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Stay near popular Sheffield attractions

Learn more about Sheffield

Tucked in the Berkshires, this charming town offers scenic hikes at Bartholomew's Cobble and local art at the Sheffield Historical Society. Catch live performances at the Berkshire Theatre Festival in nearby Stockbridge or sample farm-fresh produce at the weekend farmers' market on the town green.

FTYTP1 The Upper Sheffield Covered Bridge, Sheffield, Massachusetts, USA

Top Sheffield Hotel Reviews

More cheap stays in Sheffield

Find out more about Sheffield

Top reasons to visit Sheffield

  • Outdoor Adventures: Sheffield is a haven for outdoor enthusiasts, offering skiing, hiking, and exploring picturesque lakes and nature reserves.
  • Family-Friendly Activities: Enjoy apple picking and exciting rides, making it ideal for memorable family outings.
  • Art and Culture: Discover a variety of art galleries that showcase local talent and creativity.
  • Charming Atmosphere: Experience the warmth of friendly locals and a welcoming community in the beautiful Berkshires.
  • Diverse Accommodation: From agritourism to cosy bed and breakfasts, Sheffield has unique stays catering to every traveller.

Find great hotels near Sheffield

Experience the charm of Sheffield, Massachusetts, with a variety of accommodation options that cater to every traveller's needs. From delightful agritourism properties to inviting bed and breakfasts, Sheffield offers pet-friendly and family-oriented stays perfect for your adventure. Explore nearby attractions while enjoying a comfortable retreat in this picturesque town, with additional options available in Great Barrington for an unforgettable holiday experience.

  • Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG: This charming 3.5-star resort offers a delightful blend of leisure and adventure, making it an ideal choice for families and business travellers alike. Nestled 19.3km from Sheffield, the resort features a variety of amenities, including an onsite mini-golf course, an arcade game room, and a playground to keep children entertained. The proximity to ski shuttles and lifts ensures that winter sports enthusiasts can easily access the slopes. With spacious accommodations and family-friendly services, this resort is perfect for a memorable vacation in the Berkshires.
  • Quality Inn: Located 9.7km from Sheffield, Quality Inn is the perfect base for adventure seekers and business travellers. Guests can enjoy a range of outdoor activities, from downhill skiing to hiking and biking, all available in the surrounding areas. The hotel’s focus on adventure sports makes it an exciting option for those looking to explore the natural beauty of the region. With comfortable lodging and easy access to recreational facilities, Quality Inn caters to those with an adventurous spirit while providing essential amenities for a productive stay.
  • Holiday Inn Express Hotel & Suites Great Barrington by IHG: Situated 11.3km from Sheffield, this hotel welcomes travellers with its inclusive atmosphere and modern comforts. Known for being LGBTQIA-friendly, it provides a warm environment for all guests. The property is well-equipped for business travel, featuring meeting spaces and complimentary Wi-Fi. Guests appreciate the contemporary design and convenient location, which offers easy access to local attractions. With attentive service and a focus on providing a comfortable experience, this hotel is an excellent choice for both leisure and business stays.

Where to stay near Sheffield

Sheffield, Massachusetts, offers an enchanting blend of adventure and history, perfect for an outdoor getaway. Nestled in the beautiful Berkshires, visitors can revel in stunning scenery, charming evenings, and a family-friendly atmosphere. Nearby attractions provide a romantic vibe, with friendly locals enhancing the experience. Whether you seek thrilling activities or a relaxing retreat, Sheffield and its surroundings promise a memorable stay, complemented by some of the best hotels in the region.

  • The Berkshires: Nestled 17.7km from Sheffield, The Berkshires is a stunning region renowned for its breathtaking outdoor experiences, making it a perfect destination for adventure seekers. With a blend of scenic mountains and serene lakes, this area is ideal for skiing in the winter and hiking in the summer. The Berkshires is not only about natural beauty—it's also home to various cultural events and venues, including conferences and festivals, which attract visitors year-round, particularly in the warmer months from June to August.
  • Great Barrington: Located 9.7km from Sheffield, Great Barrington is a vibrant city that draws visitors with its dynamic outdoor lifestyle and sporting opportunities. Known for its excellent skiing facilities, this area is a favourite among winter sports enthusiasts. During your visit, explore the local parks and lakes that offer tranquil spots for relaxation and picnicking. Great Barrington sees a peak in visitors from June to August, making it an exciting summer destination that balances adventure with community events.
  • South Egremont: Just 8.0km from Sheffield, South Egremont is a charming city that invites adventure lovers to experience its ski resorts and recreational activities. This area, like its neighbours, boasts stunning landscapes featuring mountains and lakes, perfect for both winter sports and summer excursions. South Egremont attracts a steady stream of visitors throughout the year, with a notable influx during the summer months. The nearby national state park offers additional opportunities for exploration and immersion in nature.

Things to do near Sheffield

Sheffield, Massachusetts, offers a delightful mix of outdoor adventures and family-friendly activities. Visitors can enjoy skiing at local resorts, partake in apple picking, and explore various art galleries. The area is perfect for day trips and exciting rides, making it an ideal destination for memorable family outings amidst the beautiful New England scenery.

Shopping

In Sheffield, you can enjoy shopping at local gems like Hoffman's Pottery for unique items. If you're up for a drive, Lee Premium Outlets, located 22.5km away, offers a variety of brand-name stores, while the Berkshire Mountain Country Store, 24.1km away, features charming local goods.

Recreation

Lake Mansfield Park, a tranquil retreat 11.3km from Sheffield, offers serene walking trails and picturesque views, perfect for relaxation. Music Mountain, located 20.9km away, hosts vibrant concerts, while Undermountain Golf Course, 14.5km from town, provides an invigorating outdoor experience for golf enthusiasts.

Adventure

At Ski Butternut, 8.0km from Sheffield, experience exhilarating skiing amidst a vibrant sports atmosphere. The Housatonic River Walk, located 9.7km away, offers breathtaking scenery for hikers seeking outdoor adventure. For thrill-seekers, Catamount Aerial Adventure Park, 12.9km from Sheffield, features an exciting zipline and ropes course.

Nightlife

In Sheffield, the Mahaiwe Performing Arts Center offers a charming atmosphere with captivating performances just 9.7km away. Infinity Music Hall and Bistro, located 17.7km away, blends exquisite dining with live entertainment. For a rich cultural experience, the Berkshire Theatre Festival is only 19.3km from Sheffield.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Booking tips and Expedia advantages for Sheffield

To save money on your trip to Sheffield, consider visiting during the off-peak months of January and March to April, when accommodation prices are lower. Booking your stay for a Tuesday can also help you find cheaper rates, while Saturdays tend to be the most expensive. Use Expedia’s search tool to filter by budget, location, and hotel type, including eco-certified options. You can further save by bundling your hotel, flights, and activities into a package deal, ensuring you get the best value for your stay.

  • The most and least expensive months on average to stay in a hotel: The cheapest months to stay in Sheffield are January and March to April, where the prices are slightly lower. This is in comparison to July to August and October, where prices are slightly higher.
  • The most and least expensive days on average to stay in a hotel: The least expensive day to stay in Sheffield is Tuesday. The most expensive day to stay in Sheffield is Saturday.
  • Find cheap hotels on Expedia: Expedia’s search tool enables you to set your budget, choose your ideal location, and much more. You can arrange your search results to display prices from lowest to highest, allowing you to find the most affordable hotels first. Additionally, you can refine your choices by hotel type; for instance, selecting the Eco-certified filter will showcase sustainable and environmentally friendly hotels available for booking.
  • Consider bundling your trip: You can save money by combining your hotel reservation in Sheffield with your flights and activities through an Expedia package.

Find the best attractions near Sheffield

Sheffield, Massachusetts, is an excellent destination for adventure seekers and outdoor enthusiasts, offering a variety of activities such as skiing and exploring nature. Visitors can enjoy nearby national parks, nature reserves, and picturesque lakes, making it ideal for eco-friendly experiences. Whether you’re hiking, skiing, or simply soaking in the natural beauty, Sheffield promises an unforgettable outdoor vacation.

  • Bash Bish Falls State Park: Located 11.3km away from Sheffield, this stunning park features breathtaking waterfalls surrounded by lush greenery. It offers a perfect blend of adventure and tranquillity, with hiking trails that lead you through picturesque landscapes.
  • Housatonic River: Just 9.7km from Sheffield, the Housatonic River is a serene spot ideal for picnicking and scenic walks. Its beautiful banks provide a peaceful atmosphere where you can enjoy the natural beauty and perhaps spot some local wildlife.
  • Three Mile Pond Wildlife Management Area: Only 3.2km from Sheffield, this nature reserve is an eco-friendly haven. It's perfect for outdoor enthusiasts seeking adventure, with opportunities for birdwatching and exploring diverse habitats.

Best time to go to Sheffield

The best time to visit Sheffield is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are average and weather is mostly cloudy with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January23.2°F (-4.9°C)Light RainMostly CloudyAverageSlightly Low
February24.8°F (-4.0°C)Light RainMostly CloudySlightly LowAverage
March32.5°F (0.3°C)Light RainMostly CloudyAverageSlightly Low
April44.2°F (6.8°C)Light RainMostly CloudyAverageSlightly Low
May55.9°F (13.3°C)Light RainMostly SunnyAverageAverage
June63.7°F (17.6°C)Light RainMostly SunnySlightly HighAverage
July69.8°F (21.0°C)Light RainMostly SunnySlightly HighSlightly High
August67.8°F (19.9°C)Light RainMostly SunnyAverageSlightly High
September60.8°F (16.0°C)Light RainMostly SunnySlightly HighAverage
October49.8°F (9.9°C)Light RainMostly SunnyAverageSlightly High
November37.8°F (3.2°C)Light RainMostly SunnySlightly LowAverage
December29.7°F (-1.3°C)Light RainMostly CloudySlightly LowAverage

The nearest major airports for your trip to Sheffield

To visit Sheffield, Massachusetts, you can fly into several major airports. Hartford, CT (BDL-Bradley Intl.) is 59.5km away, with nearby hotels such as the Sheraton Hartford Hotel at Bradley Airport and The Capitol Hotel, both offering convenient access via airport shuttles. Albany, NY (ALB-Albany Intl.) is 80.5km distant, featuring hotels like Oakcliff Bed and Breakfast and Four Points by Sheraton Albany, easily reachable from the airport. Finally, Newburgh, NY (SWF-Stewart Intl.) is 91.7km away, with options like The Crossroads Hotel and Comfort Suites Fishkill, both accessible via local transportation services. Each airport provides a variety of accommodation choices to enhance your stay.

Frequently asked questions

Where is the best place to stay in Sheffield?
Wilder House Berkshires is one of the top choices for your stay based on our traveller data. This B&B offers free breakfast and free parking. Two other options for your trip to the area are The Yankee, Trademark Collection by Wyndham and Berkshire Mountain Lodge. See all available top hotels, or vacation rentals in Sheffield.
If I need to cancel my hotel reservation in Sheffield, will I receive a refund?
Yes, the majority of hotel reservations are fully refundable provided that you cancel prior to the hotel's cancellation deadline, which in most cases is within 24 or 48 hours of your arrival date. If your reservation is non-refundable, it may still be possible to cancel it and be given a refund within 24 hours of booking. Filter your search by fully refundable to find flexible hotel deals in Sheffield.
What are some accommodation options with pools in Sheffield?
The Yankee, Trademark Collection by Wyndham: Provides a seasonal outdoor pool, an indoor pool and buffet. Berkshire Mountain Lodge and The Red Lion Inn are a couple of other choices that feature an on-site pool. View all hotels with pools in Sheffield.
What's it like staying in Sheffield?
Visitors can enjoy all that Sheffield has to offer, including the casinos and local tours. In Sheffield, there are 34 hotels and other accommodation options to choose from. Find out more about Sheffield.
What are the top places to visit in Sheffield?
The picturesque setting of Housatonic River and Thom Reed UFO Monument Park exemplify the area's natural beauty. A couple of additional sights to add to your itinerary are Magnolia Bluffs Casino and Three Mile Pond Wildlife Management Area. Take a look at what more there is to see and do in Expedia's Sheffield guide.
What's the seasonal weather like in Sheffield?
The hottest months are usually July and August, with an average temperature of 19°C, while the coldest months are January and February, with an average of -2°C. The snowiest months in Sheffield are January, March, February and November, with each month seeing an average of 18 cm of snowfall.

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